


No Shame

by SinQueen69



Series: Kinktober [27]
Category: Teen Wolf (TV)
Genre: Anal Sex, Blow Job, College Student Stiles, Creampie, Derek Hale Has a Big Dick, Dirty Talk, Don't copy to another site, Exhibitionism, Fake Knot, Kinktober 2019, Knotting, Oral Sex, Rough Sex, Self-Feminization, Sex Work, Size Difference, Size Kink, Stiles is kinky, Stomach Bulge, Wolf Dildo, cam boy stiles stilinski, cock riding, derek is wolf, dildo, gaping, knotting dildo, stiles had a small cock
Language: English
Status: Completed
Published: 2019-10-30
Updated: 2020-08-08
Packaged: 2021-01-12 22:33:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,155
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21233651
Author URL: https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69
Summary: Stiles’ is paying his way through college as a cam boy, good thing he has no shame.Kinktober 2019 Day 29: Sex workChapter 2- Request





	1. Chapter 1

“I have a surprise for you guys tonight,” Stiles caressed his nipples as he spoke directly into the camera that was mounted just above his laptop screen that had the website he worked for open and allowed him to see his viewer’s usernames, money and stats. 

“I got so wet buying this and I could barely keep myself from using it every night since.” Stiles arched his back, whining a bit when he pinched his nipples, making them pebble on his chest and hid a smile as he heard the ding of more money being sent his way. 

Stiles stretched his body out of view of the camera for a moment before settling back down and he licked a long stripe up the side of the thick, ridged, bulbous wolf style dildo and his small cock between his thighs twitched as numerous dings sounded out as his viewer’s got excited at the sight of the dildo. 

“It’s going to gape my little pussy so wide and I just knew that I had to show you guys that,” Stiles explained sounding so innocent as he used the suction cup base to sit it firmly in front of him and stroked it a few times. He outright whimpered when his fingers barely curled around the girth and a few more dings sounded off. 

“I better get it hard and wet hm?” Stiles shuffled around so he was on his stomach and wrapped his lips around the tapered head of the dildo. He was extremely glad his stupid hot roommate was away for the weekend otherwise this could get awkward. 

“Oh it’s so big, it fills my mouth so well,” Stiles moaned as he relaxed his mouth and swallowed down a good chunk of the dildo before he gagged and had to back off. Stiles held onto the knot like base and started to deep throat the toy, keeping his eyes on the camera as he hollowed his cheeks and gagged around the dildo. 

Stiles moaned lewdly as he lifted his mouth away from the now wet dildo, a string of saliva connecting his lips to the tip still. Stiles gave the length of the toy a long, slow lick to another ding from his laptop. 

“Should I fuck my pussy wide on this wolf cock now guys?” Stiles asked tipping his head to the side and smiled sweetly as more dings sounded out as his viewers agreed. Stiles grabbed some lube and used both hands to get the dildo so wet it was covered with it before he lifted himself onto his knees. 

“I’m so wet guys, just from sucking it my little pussy is dripping with for it.” Stiles twisted around and used his hands to pry his ass cheeks apart, showing his viewers his lube wet and twitching hole. Stiles moaned as he hooked his thumbs into the rim of his hole and pulled himself open a bit more and heat coiled in his gut as numerous dings sounded off. 

“My pussy is so tight today guys, I hope that wolf cock fits inside,” Stiles commented as he moved back around and straddled the soaking toy, letting his viewers see his small cock erect between his thighs but looking even smaller against the large, thick toy that was below it.

A few dings sounded at the size comparison and shame burned in Stiles' veins, but he loved it and gave his small cock a pump for extra measure. He hated his small cock as a teen and then discovered his niche in the world of sex and kinks and since then he had been very grateful for his small size. 

“Oh,” Stiles’ head fell back as he lowered himself slowly down onto the toy, the tapered head slid inside of him with ease but as the toy began to get wider, a burn and stretch started to build and Stiles took his time knowing his viewers loved seeing his hole spread wide.

“It’s opening my pussy up so nicely, oh God it’s so big,” Stiles whined as he arched his back and sank a bit lower onto the toy, groaning as the rough ridges of the toy rubbed against his sensitive walls. 

Stiles panted open-mouthed as he looked down at the toy between his legs and moaned in pleasure at sight of his stomach bulging from the size of the toy inside of him and he felt the faux knot press against his hole. 

“Do I look full?” Stiles asked the camera as he spread his knees wide and clenched around the toy, mewling at the action and the many dings from his viewers. 

“My cunt has never felt so full, it’s wonderful.” Stiles’ speech was slurred now but he didn’t care as he slowly began to bounce himself up and down on the toy, needing to move and his small cock bounced and swayed as it dribbled pre-cum. 

“Mmm, ahhh!” Stiles groaned as he rode the toy, letting a bit more of the fake knot inch into his expanding rim with each dropdown. 

“Do, do you think my pussy can take the wolf’s knot?” Stiles asked as he used one hand to pinch and play with his nipples while his other hand rubbed at his dripping cock. Tons of dings answered his question and Stiles let his tongue loll out as dropped himself down hard onto the toy and shouted out in a haze as the knot was pushed into him fully. His small cock squirting out his release as his body jerked and clenched around the fake knot. 

“Oh, it looks like I squirted. I couldn’t help it guys, the knot just feels so good in my cunt.” Stiles whimpered as he looked down at the mess he made of himself and the dings went through the roof as he dragged his finger through his mess and licked his finger clean. 

“I have one more surprise,” Stiles panted out as he shifted his feet wider so the camera got a good view of the dildo sitting firmly in his hole. Stiles squeezed the bottom and whined at the new sensation before he eased the knot of the dildo out of himself and it popped out wetly and that was followed with a rush of white cum. The dings increased and repeated at the sight of Stiles’ gaping and cum slick hole as Stiles spread his ass cheeks apart again to show his viewers properly.

“I figured if I’m going to get knotted I better make sure my pussy is bred properly as well.” Stiles winked as he hooked his thumbs in his rim and pushed out more of the fake cum that he had loaded the dildo up with before the video. 

“Thanks for having fun with me guys, but I think my pussy needs a good cleaning and a bit of rest so I’ll be tight for you guys next time.” Stiles smiled at the camera before he cut the video and sprawled out on the floor of his dorm room. 

His chest rose up and down as more of the fake cum oozed out of his gaping hole and his soft cock lying against his thigh. Stiles just smiled up at the ceiling, he was in a haze of bliss and he knew from all the dings he heard his paycheck from this video was going to be a good one.


	2. Chapter 2

**Summary for the Chapter:**

> Tumblr Anon: Sterek prompt-hung Derek fucking less than average Stiles, both get off on the size difference. Feminization with Stiles telling Derek “use my pussy, fuck my cunt, etc” and Derek telling Stiles to ”play with your tits.” Please and thank you😍
> 
> +
> 
> genuinedaisy on Ao3 wanted: Gosh a perfect sequel would be if Derek found it or something and is super turned on (and he's still a were). And then Stiles and him just go at it.

“Hi everyone, you’re in for a special treat tonight! I have a guest here who is going to make sure my pussy is properly wrecked by the end of the night. He goes by Wolf and boy does he live up to that nickname.” Stiles greeted his viewers, smiling innocently even as a man stepped into the sightline of the camera; a decorative wolf mask covering his face but the focus was on the long, thick, veiny cock that was starting to harden between his thighs. 

A few dings sounded off at the sight and how Stiles was already on his knees, totally naked and his small cock erect between soft looking thighs. Stiles happily nuzzled Wolf’s heavy balls, lapping at them before he dragged his cheek up the length of the man’s cock before suckling at the tip to the sound of more dings. 

“You’re so big Wolf, I can’t wait to have you in my pussy.” Stiles moaned.

“Of course you can’t, sluts like you rarely can. I’m going to fuck this dirty mouth, I’m going to make you gag and choke on my cock while you play with your tits for everyone’s viewing pleasure.” Wolf growled and a few dings sounded out, only increasing when Wolf grabbed Stiles’ head, yanking it back harshly and shoved his long cock into Stiles’ mouth. 

Instantly Stiles began to choke on the thick length, drool forming at the corners of his mouth and eyes stinging as he relaxed his jaw to let Wolf fuck his mouth the way he wanted to. Stiles placed his hands on his chest and began to pluck and twist his nipples, whining and mewling around his mouthful as the room echoed with dings, more so when Wolf alternated between fucking Stiles’ mouth with his cock and dragging his sweaty balls over his face. 

Stiles gasped openly when Wolf shifted away to inspect him and how his small cock was drooling between his thighs. Wolf grunted and grabbed a fistful of Stiles’ hair and shoved him so Stiles was on his hands and knees, facing the camera so everyone watching could see the mess of drool, salvia and pre-cum that covered his face and his puffy nipples. 

“You do have a pretty, tight little pussy here slut, by the time I’m done it will be as gaping and messy as the time rode that fake wolf knot,” Wolf commented as he tilted Stiles hips up, kicking Stiles’ feet apart until he was in the correct position. 

“Please ruin my pussy Wolf, I need a real man’s cock to wreck me properly,” Stiles begged as more dings sounded off as Wolf began to apply lube to his cock behind him. 

“Dam right you do slut, all of us have been waiting to see you be properly put in your place,” Wolf grunted as he pried Stiles’ ass cheek apart to slap the wet, fat head of his cock against Stiles’ pucker. More dings went off at his words and actions and Stiles felt humiliation and arousal burn through his body and his cock leaked further at this. 

“Please, please fuck my cunt Wolf, stuff my pussy full with your big, fat cock!” Stiles pleaded, pushing back against Wolf’s cock needily. The dings were coming faster as he pleaded and they became extremely loud as Wolf plunged his cock into Stiles, forcing Stiles to wail out his pleasure. 

Stiles’ body shook as he gasped while trying to adjust to such a large stretch in his ass. Stiles’ eyes rolled up into his head; drool dripping down his chin as Wolf began to fuck into him without so much as asking if he was ready. Ding’s echoed in Stiles’ ears alongside the sound of Wolf’s large balls smacking against his ass on each thrust. 

“Your cunt is as tight as I expected,” Wolf grunted as he dug his fingers into Stiles’ hips, lifting him higher to slam in deeper. Stiles writhed and mewled as he was opened up over and over on the man’s engorged cock. 

“Ah, ngh, p-please, more! Fuck my cunt harder, ruin my pussy with your cock!” Stiles babbled mindlessly, wailing again when suddenly Wolf changed their positions. Wolf yanked Stiles onto his lap as he sat down, Wolf grabbed and spread Stiles’ legs wide to show the people watching Stiles’ tiny cock leak as Wolf rammed his much larger cock up into Stiles’ puffy, pink hole. So many dings overlapped at the new position as Stiles was reduced to as Wolf’s fuck doll as he was pulled down onto Wolf’s cock over and over as his small cock steadily leaked. 

“Come on slut, squirt for me. Clench that cunt up around my cock and beg for me to cream it,” Wolf ordered as he roughly squeezed Stiles’ cock. 

“Come in my cunt, please Wolf, oh god please!” Stiles all but screamed as he came, spurts of white spraying from the tip as Wolf ground his cock deeper. 

“Fucking cock slut,” Wolf groaned as he stilled, cock throbbing inside of Stiles before he flooded Stiles’ insides with his cum. Stiles sobbed when Wolf let his cock slip out of Stiles’ now messy hole before reaching down and spread Stiles’ ass cheeks wide to show the camera his sloppy hole and the room exploded in dings. 

“Thanks for watching Wolf wreck my pussy and make me realize what a slut I am,” Stiles slurred in goodbye to his very happy and generous patrons before shutting down the camera.


End file.
